3993+ Vacation Rentals Near Lollapalooza |
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Sell Off Cruises - Vacation Rentals in Lollapalooza

Mccomick Place/China town getaway From US $338
         

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New
Apartment
Mccomick Place/China town getaway
  • Parking
  • Pet Friendly
  • Child Friendly

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The Sono Chicago From US $262
         

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10.0 (530 Reviews)
Bed & Breakfast
The Sono Chicago
  • Air Conditioner
  • Parking
  • TV

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4BR Old Town Chicago Loft | Walk to Wells St From US $836
         

10.0 (124 Reviews)
Apartment
4BR Old Town Chicago Loft | Walk to Wells St
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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New Luxury 3 Bdr Apt in Chicago C9 From US $1,516
         

10.0 (1 Review)
Apartment
New Luxury 3 Bdr Apt in Chicago C9
  • Air Conditioner
  • Parking
  • Pool

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The Publishing House B&B From US $327
         

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9.8 (209 Reviews)
Bed & Breakfast
The Publishing House B&B
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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3 BD condo near to downtown, Gold Coast and Michigan Avenue. From US $358
         

9.6 (27 Reviews)
Apartment
3 BD condo near to downtown, Gold Coast and Michigan Avenue.
  • Air Conditioner
  • Parking
  • TV

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Stunning 1 bedroom Apartment with Full Amenities by C9 From US $653
         

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New
Apartment
Stunning 1 bedroom Apartment with Full Amenities by C9
  • Air Conditioner
  • Parking
  • Pool

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52nd Floor MagMile Penthouse Views Fireplace Pool From US $313
         

10.0 (413 Reviews)
Apartment
52nd Floor MagMile Penthouse Views Fireplace Pool
  • Air Conditioner
  • Parking
  • Pool

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51st Floor MagMile Penthouse Views Balcony Pool From US $313
         

10.0 (233 Reviews)
Apartment
51st Floor MagMile Penthouse Views Balcony Pool
  • Air Conditioner
  • Parking
  • Pool

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LOCATION! Mins to downtown! Fulton mkt/Noble Square, FREE PARKING & LAUNDRY From US $268
         

9.6 (22 Reviews)
Apartment
LOCATION! Mins to downtown! Fulton mkt/Noble Square, FREE PARKING & LAUNDRY
  • Air Conditioner
  • Parking
  • TV

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Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC From US $261
         

10.0 (364 Reviews)
Apartment
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
  • Air Conditioner
  • Parking
  • TV

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3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place From US $320
         

10.0 (308 Reviews)
Apartment
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
  • Air Conditioner
  • Parking
  • TV

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1F Chicago's Little italy Graystone nearDowntown From US $352
         

10.0 (196 Reviews)
Apartment
1F Chicago's Little italy Graystone nearDowntown
  • Air Conditioner
  • Parking
  • TV

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52nd Floor Penthouse with Skyline Views and Pool From US $293
         

10.0 (67 Reviews)
Apartment
52nd Floor Penthouse with Skyline Views and Pool
  • Air Conditioner
  • Parking
  • Pool

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Luxury House in the heart of Old Town with Parking From US $1,995
         

10.0 (60 Reviews)
House
Luxury House in the heart of Old Town with Parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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Brilliant Downtown Chicago 3-Bedroom Condominium From US $488
         

10.0 (55 Reviews)
Condo
Brilliant Downtown Chicago 3-Bedroom Condominium
  • Air Conditioner
  • TV
  • Balcony/Terrace

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50th Floor Mag Mile Views, Balcony, Pool, Gym From US $236
         

10.0 (42 Reviews)
Apartment
50th Floor Mag Mile Views, Balcony, Pool, Gym
  • Air Conditioner
  • Parking
  • Pool

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Vibrant 3BR Pilsen Stay Free Parking Near Downtown From US $272
         

10.0 (40 Reviews)
Apartment
Vibrant 3BR Pilsen Stay Free Parking Near Downtown
  • Air Conditioner
  • Parking
  • TV

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Gorgeous 3BR River North Condo - Free Parking From US $795
         

10.0 (39 Reviews)
Condo
Gorgeous 3BR River North Condo - Free Parking
  • Air Conditioner
  • TV
  • Security/Safety

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Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable. From US $3,346
         

10.0 (36 Reviews)
House
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
  • Air Conditioner
  • Parking
  • Pet Friendly

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City Center, River North Condo HUGE 3BR, Patio, Parking(2x) From US $845
         

10.0 (35 Reviews)
Condo
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
  • Air Conditioner
  • Parking
  • TV

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Luxury Loft Collection 703 - Terrace - River North From US $685
         

10.0 (29 Reviews)
Apartment
Luxury Loft Collection 703 - Terrace - River North
  • Air Conditioner
  • Parking
  • Pet Friendly

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Modern West Loop Gem-City Views & Prime Location 6 From US $643
         

10.0 (26 Reviews)
Apartment
Modern West Loop Gem-City Views & Prime Location 6
  • Air Conditioner
  • TV
  • Security/Safety

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Spacious 4BR Central Apartment w/Skyline Views From US $334
         

10.0 (26 Reviews)
Apartment
Spacious 4BR Central Apartment w/Skyline Views
  • Air Conditioner
  • Pet Friendly
  • TV

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★ Pro Tip: Selloffcruises makes it easy to compare the best listings on Selloffcruises homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Selloffcruises homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Lollapalooza.

Weather in Lollapalooza

View the weather forecast for Lollapalooza before booking your Lollapalooza Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Lollapalooza, IL

Selloffcruises offers a large selection of top attractions around Lollapalooza. Research things to do on your vacation before you visit Lollapalooza.


Navy Pier Wrigley Field McCormick Place Millennium Park Union Station Soldier Field Willis Tower Art Institute of Chicago United Center Grant Park John G. Shedd Aquarium Chicago Museum of Science and Industry Chicago Theatre Chicago Riverwalk Field Museum of Natural History University of Chicago Brookfield Zoo John Hancock Center Lincoln Park Zoo Water Tower Place

Lollapalooza Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Lollapalooza?

Currently, the total number of properties listed in 2026 is over 3993 in the Lollapalooza area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Lollapalooza.